Sissy Shopping

This carries on for some time, man after man filling Katie with cum who is now plastered over her face and has jism all down her stockings and over her dress. Some of it has even gone as far as her pretty shoes, shining in the light. You can't remember how many men she has had, nor how many times you've felt extra cum lube being shot up your ass, or how often you've had to endure the severe pain in your nipples followed by the wonderful sensations in your clitty. All you can think of is being fucked hard by your mistress Maria, you desperately want to cum in her mouth, her pussy, her ass, her face, her shoes, her panties, her hair, anywhere, you just don't care if you are just allowed to finally orgasm. Around this time the video suddenly cuts out, and you are once again plunged into darkness and tranquillity as all the dildos and pleasure devices stop and withdraw completely. Your head phones are lifted off and you feel Maria's breath on your ear and now oh-so-sensitive neck.

"Hey there sweetie, are you having fun? How do you like Katie? She was a lot of fun. I hope you'll be just as much fun as she was before I had to let her go. All those men! You wouldn't think a girl could take that much cum, but you sissies really are a breed apart. You'd do anything for your Mistress wouldn't you?"

You feel a rubber clad hand slide into your panties, stroking you between your thighs before gradually exploring upwards.

"You want to be a good girl for Maria don't you? You want your special reward? I bet you'd love to cum right now. Do you want me to milk your tiny little, pathetic excuse for a wee-wee? I've fucked dykes with more impressive clits than yours. But I'll make sure you have a very happy ending tonight so long as you stay good and do what your mistress demands. Now then, I've finished getting my strap-on collection ready for you. So I'm going to stop the Sissy Fucker from playing with your cute little bot bot and I'm going to use it instead. I'll also be switching that lovely cock in your mouth to gag mode so you'll get to enjoy that so much more when it's in your throat. Oh one last little present before I start."

You hear Maria's heels tapping across the floor again, making your cock twitch in your panties as you remember those amazing thigh length boots with the metal heels. You so want to play with them, running your mouth and tongue over the dark leather before taking the heels in your mouth and letting Maria fuck you with them like little metal cocks. You hear her stop in front of you and then a slight rustle as she kneels down until she is face to face with you. The blindfold screens are flipped up and you are greeted with the close up view of Maria's face as she spits a huge gob of spit right in your face! The last thing you see is a grin on her face before she flips the screens back down and replaces your headphones. You can feel her spit running down your face, down your nose and then into your mouth where the gag makes a gap. You feel a shiver go through your body, starting at your panties as you taste Mistress for the first time.

"Hello Sissy." you hear through the speakers, in a very girlish baby talk voice.

"This is your intermission. I'm sure you must be thirsty by now after all those winkles you've been sucking, so I've prepared a little drinkywinky for you. Now, be careful not to spill any or your punishment will be even worse this time. I'm serious..." back to her stern voice, "one drip and what I make you eat for dinner will be far worse..."

Maria continues in her baby talk voice "Now little sissy needs to drink from her botty to grow up big and strong, oh I'm sorry Sissy, your little dicklet is never going to do that is it? Poor little Sissy with her tiny excuse for a penis. Never mind though, you'll get to play with lots of big hard, woman pleasing cocks soon, they just won't be yours. *laughs* Anyway, I was telling you about your special drinkywinky. You are to take the nice big winkle in your mouth and then suck down all the goodness inside. I especially made it for you! If you are quick it will still be warm, and every little sissy likes warm, wet things. Now drink up!"

Another dildo is slid into your mouth and the gag is released allowing you to close your mouth again, an absolute relief. At least it would be if you didn't have this huge cock between your lips. Oh well you think, I am actually rather thirsty after dribbling down my dress top all evening. I hope it's nice.

"Time to start sucking your juice now Sissy, sucky wucky woo! Yum yum yum! I want to see a nice empty bottle in 60 seconds otherwise it will be punishment time again! 55 seconds now!"

Hearing this you quickly start sucking on the cock but nothing much seems to be happening. You suck as hard as you can and are then finally rewarded with your first squirt as you hear Maria count out that only 45 seconds are remaining. With no idea how much you are expected to drink you keep sucking it in to your mouth until finally you have to stop to swallow. At this point the frantic messages from your tongue telling you what it is you can taste finally flood through and you realise you've been drinking Maria's warm piss! At least you hope it is Maria's you think, memory suddenly going back to that line of men fucking Katie. With no option what to do and your tongue still swirling about in the warm golden amber that Maria has given you to drink, you gulp it all down and start sucking again.

"Only 20 seconds to go sweetheart, I hope you are enjoying your drinkywinky. Like I said, I made it myself today just for you! I really hope you are enjoying my piss, you are extremely privileged really. Many men would pay me for my fresh piss squirted in their mouths and here you are getting it for free. 10 seconds to go! Not long til your punishment I think... 5 seconds... 4, 3, oh dear!, 1..."

With one mighty gulp you suck the cock dry and swallow the last of Mistress's piss.

"Good girl Sissy! It looks like you managed to take all of my gift in time. A little reward is in order I think, I hope you like it."

The cock is slid back out of your mouth, leaving you feeling a little empty. Finally released from oral torment after so long you start to run your tongue around your mouth to restore some feeling. You then feel your headphones and blindfold being removed again, once more revealing the beautiful face of your Mistress smiling at you.

"You are such a well behaved little slut aren't you? Imagine drinking all my piss like that, you must be a real little whore. No normal person would be happy to suck my piss out of a rubber dildo forced in their mouth and then gulp it down but you did it with such energy that I'm going to give you a little present. Now, give me a kiss..."

Not fully trusting Maria after what happened when Katie was offered a kiss, you keep your eyes open and watch as Maria brings her face closer to yours. Her eyes closed and mouth slightly parting, you are fixated on the bright red colour of her lip gloss as it approaches your own pink painted lips. You catch a brief glimpse of her tongue moving forwards in her mouth towards her open lips and just peek out, before closing your eyes and accepting her sweet kiss. You breathe in, wanting to absorb all of this captivating beauty and smell her scent, a delicious combination of her perfume and obvious excitement. Her lips meet yours and you feel a tingle go through your body, you can't believe how excited one kiss can make you feel! Your lip gloss merges and you feel her breathe out slowly into your mouth as her tongue probes forwards, darting in to your mouth and locating your more passive tongue. The feelings in your body feel if anything more exciting than when she was playing your sissy clitty, and you never want it to end. You breathe in again, absorbing her breath into your body as she runs her tongue around your mouth tasting every last bit of you. Her gloved hands touch the side of your face, lovingly caressing you with the cool touch of the material on your hot skin. Then she is gone... The sense of loss is unbearable and you instinctively reach out with your tongue to find her again but no more is to be had.

Your blindfold, headphones and gag are all swiftly replaced leaving you reeling in your once more sensory deprived state. All you can feel is an overwhelming desire to do everything you can for Maria, your first true girl friend. She must be your girlfriend by now surely? No girl would kiss you like that without meaning it? Yes of course, Katie was silly to have thought differently, she must have not done everything Maria desired which is why she's no longer around. Hah, stupid girl you think, who would give up somebody as perfect and caring as Maria?

As you are thinking this, Maria was getting ready for the finale of tonight's activities. She slid the dildo gag back in to the grateful mouth of her latest Sissy money spinner and smiled. Touching up her lip gloss, she thought about Sissy's credit card and how pathetic it was. Almost as pathetic as her dick, she mused. Schedule running to plan, Sissy should be feeling extreme desire for her now and would be willing to do anything for her mistress. That would be tested tonight. If Sissy does well, she'll be kept for a while as a pet, if not... She won't be the first sissy left still dressed in drag dumped in the car park of a seedy nightclub down town. But back to tonight, I still have lots to do.

Starting up the machine again, sans anal play this time, Sissy suddenly found her kiss related excitement ripped away from her as her nipples were once again viciously sucked and bitten by her machine.

"Those nipples are growing nicely already." Maria chuckled to herself.

Leaving the room and Sissy already having her little dicklet massaged back to life, she went to the next room along and checked all the cameras. They all looked fine, and other than a couple of minor adjustments to centre some pictures it would all be perfect for the evenings *real* entertainment soon to begin. Maria adjusted the rear camera and took a nice zoom in of Sissy's gaping ass, lubed up and ready. Ready for my strap-on, Maria thought, shame that isn't what she'll be getting.

With that done Maria re-centred the camera and headed back to the sissy fucking room.

Chapter 6

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You find yourself back watching Katie getting fucked again, almost drowning in the amount of cum she has drunk and is covered in. You are sure some of the men that had already been had rejoined the queue on the other side and were willing to go again. At this rate she might go on taking cock forever! After a while, however, she was given a reprieve and instead the men were shooed off other than the two that were still going.

"Fuck that cunt harder!" you could hear Maria telling the one with his really rather huge cock rammed to the hilt in Katie's ass. He responded to her command and start really reaming her, causing her body to shake back and forth in her harness. You can hear Katie squealing loudly now, obviously in some pain from the brutal ass rape she is receiving. Maria then takes hold of the cock in Katie's mouth in her hand, expertly stroking it in her gloved hands. She directs his cock directly at Katie's face and with two more jerks he explodes hot jism smack into her face. Some of it goes up Katie's nose, some in her eyes, some in her mouth and the rest all over, adding to the gooey white mess already decorating the extremely used sissy.

Maria then begins the slow process of pushing all that cum into Katie's still open mouth, who gulps it down quickly as Maria tells her what a good girl she is. The man fucking Katie's ass also cums while watching Maria playing with Katie's face cum, and shoots one last load of cum deep into her rectum. The site of Maria on screen again is really exciting, and watching her jerk that cock off into Katie's face is incredibly horny, but you have learned that over-excitement leads to pain. Even with the blow-job sensations, you have now been conditioned over several hours not to get too excited without Mistress's command. You instead just continue to enjoy the show and the dildo fucking your mouth while your clitty is gently stroked, sticking slightly out of your panties. Your nipples are being gently tickled too which is a lovely feeling as your still somewhat gaping ass drips lubricant down the seams of your stockings.

The dildo in your mouth is, true to Maria's word, now definitely in a more aggressive mode. It seems to be moving gradually deeper with each stroke and is already just barely touching the back of your mouth. You hope Maria comes back soon, and you are sure Maria will rescue you before it gets too painful. On screen, Maria is still feeding cum to Katie, scraping it across the sissy's face with her rubber clad fingers before pushing them in to her mouth to be cleaned by Katie's tongue. In and out went her gloved fingers, Katie greedily licking up all the mess that her Mistress was feeding her. You feel jealous of her treatment, wishing you had Maria's fingers in your mouth instead of the dildo, but you continue to watch desperate to find out what happens next.

While this continues to happen, you feel pressure up against your sissy rose bud, much more than before and you realise it must be Mistress with her strap on at last! You feel a warmth go through you as you realise how lucky you are to have such a thoughtful Mistress. She must have known you would be feeling jealous of Katie's intimacy with Maria and was now rewarding your patience with her loving cock. It is much bigger than the one you have had inside you for so long, and softer somehow although still very firm. Maria slowly enters you, not wanting to hurt you, just pleasure you with her beautiful penis as she slides it further inside the anal slut hole in the back of your nice, new frilly pink panties that Mistress had helped you buy yesterday. She fills you more and more, making you squeal with pleasure, and you feel a little stroke on your clitty. Was that the machine again? You are sure those were real fingers that time, Mistress Maria must be very happy with you! Now she seems happy with the tightness of your ass and she begins a nice slow rhythm, fucking you in and out, in and out, almost matching the beat of the penis gag still fucking your mouth. You feel the nipple clamps sharply pulled off and make loud squeaking noises around your gag as feeling is suddenly returned to your long suffering nipples. This is quickly forgotten however as the hand returns back to your panties and starts stroking your little peepee again.

Making little high pitched squeals of delight, you begin to really enjoy your Mistress's attention as she builds up speed, now starting to fuck you quite hard. The Sissy Fucker Chair you are strapped to starts to shake a little with the momentum of each thrust that your tiny, tight sissy pussy takes, almost hard enough to force you more on to the penis gag still raping your mouth. This has now definitely moved a little further in you are sure, but it is still relatively comfortable and you love the full, warm loving feeling of having Mistress inside you from both ends.

On screen, Maria now seems to have finished feeding Katie the last of the cum and then places her gag back in before inserting a ball gag as well. She then walks sexily round behind her sissy, making a point of bending over in front of the camera and showing off her fabulous long legs, beautiful boots, sexy stockings and wondrous ass. She picks up a large butt plug from the floor, moves further round behind Katie so as not to obstruct the video and positions it at Katie's sissy pussy.

"Now be a good girl for me and take your plug like a good little whore. You wouldn't want to lose any of that cum I've just studded inside you would you?" Maria asked Katie, who wriggled around in anticipation.

Stopping briefly to scrape up as much cum from Katie's stockings as she could, she pushes it into her ass with her fingers to lubricate the way for the imposingly large plug. Once satisfied with the amount of cum she can fit in, Maria begins to slide the big, silvery metal plug home.

It must be a little cold, as Katie shivers slightly before raising her pert, cute, girly bottom as high as she can to make it easier for Maria. It goes in easily at first, well lubricate with the cum of several dozen men, but very quickly increases in width and even Katie's recently gang-raped pussy starts protesting. Maria reaches down, slides one her hand inside the frilly edges of Katie's yellow knickers and being stroking her little dicklet as she pushes harder on the plug. Katie is now obviously feeling the size of the anal invader that is being inserted roughly into her, and starts to make cute little squeaking noises through her gag.

"Oh shut up you stupid whore, your cunt belongs to Me and I will fuck it with anything I please. You are to take everything I give you, and thank Me for it."

This doesn't seem to stop Katie struggling as Maria rams the enormous plug further in. You can see it is almost at the widest point when Maria removes her hand from Katie's undies and instead uses both of her arms, still wearing those fabulous black latex gloves, to hammer it in the remainder of the way. Katie shrieks in pain as it finally fully enters, her stretched anal muscles now pulling in the rest of the plug as it tapers off to the base.

"There you go, that's better isn't it? Don't you see how much better things are when you do what I say? Such a shame that you obviously never learned your lesson before though. You started seeing that other girl behind my back, and I punished you. I sent her that video of you dressed in that pretty white wedding dress, make up all so perfect, before you were gang raped so happily by all those men. My favourite bit was when I had you tell me how much you loved me, and how you'd never cheat on me, and how much you loved being fucked by men for me. Such a shame that your girlfriend didn't enjoy watching that as much as I did. But I was incredibly forgiving and took you back, although you did receive many punishments. It must have been awfully trying to sit in your chair at work after having been caned so many times each morning. Even if I did let you wear my silky panties to help soothe your poor bottom. But you did make me a lot of money with all the cocks you took."

As Maria continued to talk, describing more of the ways she had punished Katie for her earlier infraction, you feel a change in the way that your ass is being fucked. Maria speeds up a little and then she stops as you feel squirt after squirt of lubricant shot up your sissy pussy. Mistress is so good to me, you think, she wants to make sure I can enjoy her all night long and is keeping me properly lubricated. It must have cost a lot to have all these special strap-ons made with built in lubrication. No wonder she had to have Katie raped by so many men, I hope they paid enough that I won't have to and I get to just serve my wonderful Maria.

E

Mistress then pulled out and a minute or so later, after which the cock in your ass is replaced by Mistress's next strap on. A little bit of cum lube had just started to run out of your sissy hole, and you can feel fingers scooping it up and pushing it back in before sliding the firm but soft penis in. You've had a few butt plugs inside you before when you've been alone at home playing dressing games, but these feel so much better. You know your Mistress loves you when She has such beautifully made soft loving cocks to fuck you with.

You are taken hold of again, this time by pulling on your harness, as Maria continues to talk to Katie.

"After all those punishments I thought you would have learned your lesson. But what did I find out a few days ago?"

Katie begins squirming around again, obviously distressed at the turn of conversation.